Literature DB >> 25893894

Pt-catalyzed rearrangement of oxaspirohexanes to 3-methylenetetrahydrofurans: scope and mechanism.

Christian A Malapit1, Sampada M Chitale1, Meena S Thakur1, Rosa Taboada1, Amy R Howell1.   

Abstract

A novel Pt-catalyzed rearrangement of oxaspirohexanes to 3-methylenetetrahydrofurans is reported. Mechanistic studies by (13)C-labeling experiments confirm oxidative addition of Pt(II) regioselectively to the least substituted carbon-carbon bond of the cyclopropane to form a platinacyclobutane intermediate. To our knowledge, this is the first alkoxy-substituted platinacyclobutane that has been observed spectroscopically. The scope and a proposed mechanism of this new Pt-catalyzed transformation are described.

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Year:  2015        PMID: 25893894     DOI: 10.1021/acs.joc.5b00604

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  2 in total

1.  Pd-Catalyzed Acyl C-O Bond Activation for Selective Ring-Opening of α-Methylene-β-lactones with Amines.

Authors:  Christian A Malapit; Donald R Caldwell; Nicole Sassu; Samuel Milbin; Amy R Howell
Journal:  Org Lett       Date:  2017-04-04       Impact factor: 6.005

2.  Theoretical Study on the Mechanism of Rearrangement Reactions of Bicyclic Derivatives of Cyclopropane to Monocyclic Derivatives under the Catalysis of Pt-Salt.

Authors:  Arpita Chatterjee; Sonjoy Mondal; Rohini Saha; Poulami Pal; Kuheli Chakrabarty; Gourab Kanti Das
Journal:  ACS Omega       Date:  2018-11-28
  2 in total

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